Ethylenediamine → 1-phenethyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea

HRID 905928Notes

Reaction equation

HRID 905928 reaction equation
[CH2:1]([NH:9][C:10]([NH:12][C:13]1[N:14]=[C:15]2[CH:21]=[CH:20][N:19](COCC[Si](C)(C)C)[C:16]2=[N:17][CH:18]=1)=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N)CN>CN(C)C=O>[CH2:1]([NH:9][C:10]([NH:12][C:13]1[N:14]=[C:15]2[CH:21]=[CH:20][NH:19][C:16]2=[N:17][CH:18]=1)=[O:11])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 593633651-phenethyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Product 1

HCID 462354781-phenethyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-ureaYield 26.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-phenethyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.22 g, 0.53 mmol), tetrabutylammonium fluoride (1 M in THF, 3 mL, 3 mmol) and ethylene diamine (0.3 mL, 5 mmol) in 5 mL of N,N-dimethylformamide was stirred at 80° C. for 14 h, then concentrated. The resulting residue was triturated with methanol then ether to afford 0.040 g (26%) of 1-phenethyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-urea as an off-white solid.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was triturated with methanol

Sources & evidence

ORD record
ord-b39a64dddc4c4ffab259099f727019fc
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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